How am I going to back this thing up alone?! How Drew Bensen Started Full-Timing

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The more we travel across America, the more awesome people we meet on the road. That’s why each month we’re posting interviews with some of our favorite RVers.

In this post we’re talking to Drew Bensen, who we met back in February at our RV Entrepreneur Summit. Drew runs Close to Home Pet Services, a dog-walking and pet-sitting company based in the Seattle area.

In this interview we talk about…

  • How Drew was drawn to the RV life
  • How he chose a Winnebago travel trailer
  • The biggest problem he’s encountered while running his business on the road
  • His most meaningful experience on the road

Introduce yourself! 

My name is Drew Bensen. I am an entrepreneur, author, public speaker, empowerment coach. In November 2016 I moved into a 2017 24’ Winnebago travel trailer. I live with my dog Ralphie.

Where are you right now?

I am in Seattle, Washington currently. This is the longest I’ve chocked the wheels since I started. Landed here July 9th and plan to stay through September. The summer in Seattle is epically gorgeous, like love-at-first-site, ask-her-to-marry-you dreamy.

Unfortunately there are very few options for RV parks near the city. I’m parked in a friend’s driveway about 30 minutes from downtown.

What inspired you to move into a trailer and start traveling the country?

Beginning of 2016 the ideas kept coming to me to travel and ‘inspire’. I didn’t have a word for it or give the idea too much mind time. Being an entrepreneur I’m used to ideas, inventions, concepts coming to me. I can’t keep them all. It would drive me mad. This one was persistent though. One day I was in my mastermind entrepreneur group and I turned to my mentor and asked her. “If I buy an RV, will you travel with me and do the Inspiration Station?” (The name is already taken) She said yes.

I tabled it after going to RV shows and dealerships. I didn’t see realistically how I could ‘afford’ it.  A few months went by and I woke up around 3 am. Shot right up and knew I need to buy an RV and travel around. My gut told me to. Two months later I had a new truck and RV.

What kind of RV did you pick and why?

I chose a 24-foot (I think its a 241rg) travel trailer and F-150 Truck.

I kept my eye on the Winnebagos because of quality, weight, and mostly they are attractive inside and out. Also wanted to be able to park, detach and be able to drive the truck anywhere without size restrictions. I love the floor plan I have because of several features. The two outside doors, the two doors in the bathroom and the bedroom in the rear with a shutting door. This has made having guests in a 24 foot space doable. I felt like working from ‘home’ would be challenging if my bed was in the same room. I sit at my dinette to do most of my work. This trailer has just enough psychological space for me.

What’s the biggest challenge you’ve encountered running your business remotely?

The biggest challenges I have are finding wifi or cell service. I have had to plan my landing locations around cell service. For the first 10 months of this adventure I had a second consulting job as a software sales rep. I needed to have service and wifi in order to have skype video meetings and phone calls all over the globe. In July I amicably parted ways with that company.

I am now in Seattle working with my company restructuring a few things. When I hit the road again I will be able to journey without ‘needing’ service every day.

Watch out adventures, here I come.

How do you plan where you want to travel to next?

When I leave Seattle I am taking my sister Tami on an adventure. Again I won’t need to work every day so I can travel to places without cell signals. We are going to let the universe take us on a trip. Relax my caring friends, I’ll check weather reports, I’m not trying to encounter snow or ice. We are going to go in whatever direction feels right. She’s an artist so this could be hippy dippy. I’ll keep you posted on the adventure.

What does your office set up look like?

Currently my office is a coffee shop/ bookstore in Seattle’s Seward Park neighborhood.

In my rig I sit at my dinette. I sit on a meditation pillow on top of the bench cushion. Sitting on your butt for hours can not only hurt but throw your whole body off. The pillow keeps my back straight and I’m sure it keeps me zen.  I use my iPhone, Macbook pro, and beats head set on the technical side. The big headset with pillowy cushions on my ears like I’m a baller headed to the big game. This headset is perfect for calls. Try it, you’ll never go back to those in your ears headsets.

What was your biggest fear before jumping into RV life and how did you move past it?

Taking the leap to get rid of everything and know everything would work out. I had no idea how it would work just that I thought it would and here I am 11 months later.

But once I bought the rig the fear became, How am I going to back this thing up alone?

What’s been the most difficult part of transitioning into full-time travel?

The best and hardest part has been adjusting to so much alone time. I enjoy my alone time but sometimes this lifestyle creates isolation. I have made a conscience effort to engage with folks when I want to and have alone time when needed. Also apparently I love to shop. I’ve had to rethink my retail therapy tendencies. Don’t judge, we all have something.

The second thing I am challenged with is being away from the beach. I lived in Seal Beach, California prior to ‘leaving it all behind’. I miss the ocean and that atmosphere. If I could, I would park my RV everyday where I could sit next to the ocean waves. That comment may get me kicked out of the full time RV cool kid club.

What has been your most meaningful experience so far?

Connecting with people. From taking my Grandma on a 4 week road trip to getting my parents to come ‘camp’ with me. This lifestyle has opened doors for me I knew were there, but didn’t have access to. I’ve met hundreds of people, attended several conferences, wrote a blog, wrote a book, had a photo shoot and book promo in LA, became certified as an empowerment coach, started my public speaking career, was a caregiver to a relative post surgery and visited more family and friends than a had over the last decade. I did all of that and more in 10 months. (No wonder I’m tired.)

Where can people follow your adventure?

Want to meet up with us on the road? Join us (& Drew!) at the 2018 RV Entrepreneur Summit! 

Read More Interviews with Full-Timers:

Make Money RVing: How to Make $100,000 a Month Blogging

Why This Couple Is Traveling to All 50 States in a Renovated Winnebago

RVE 004: 7 Ways to Build Remote Income And Make Money While Traveling


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